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L-Rhamnose (M2MDB003467)

Record Information
Version2.0
Creation Date2012-10-10 12:15:07 -0600
Update Date2015-06-03 17:25:52 -0600
Secondary Accession Numbers
  • ECMDB23077
Identification
Name:L-Rhamnose
DescriptionRhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of certain bacteria. L-rhamnose is metabolized to L-Lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. It exists in two anomeric forms, alpha-L-rhamnose and beta-L-rhamnose.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-Deoxy-L(+)-mannose
  • 6-Deoxy-L-Mannopyranose
  • 6-Deoxy-L-mannose
  • 6-deoxy-Mannose
  • 6-Deoxyhexopyranose
  • 6-deoxyhexose
  • 6-Deoxymannose
  • Isodulcit
  • Isodulcitol
  • L(+)-Rhamnose
  • L(+)-Rhamnose monohydrate
  • L(+)-Rhamnose monohydric acid
  • L-(+)-Rhamnose
  • L-(+)-Rhamnose 1-hydrate
  • L-(+)-Rhamnose 1-hydric acid
  • L-(+)-Rhamnose Hydrate = 6-Deoxy-L-mannose Monohydrate
  • L-(+)-Rhamnose hydric acid = 6-deoxy-L-mannose monohydric acid
  • L-(+)-Rhamnose monohydrate
  • L-(+)-Rhamnose monohydric acid
  • L-Mannomethylose
  • L-Rha
  • L-Rhamnopyranose
  • L-rhamnose for biochemistry
  • L-Rhamnose Monohydrate
  • L-Rhamnose monohydric acid
  • Locaose
  • Mono(6-deoxy-b-L-mannopyranosyl) ester
  • Mono(6-deoxy-beta-L-mannopyranosyl) ester
  • mono(6-Deoxy-β-L-mannopyranosyl) ester
  • P-(6-deoxy-b-L-mannopyranosyl) ester
  • P-(6-deoxy-beta-L-mannopyranosyl) ester
  • P-(6-Deoxy-β-L-mannopyranosyl) ester
  • Rhamnopyranose
  • Rhamnose
  • Rhamnosemonohydrate
  • Rhamnosemonohydric acid
  • UDP-rhamnose
  • Uridine 5-pyrophosphate
  • Uridine 5-pyrophosphoric acid
  • Uridine diphosphate rhamnose
  • Uridine diphosphoric acid rhamnose
Chemical Formula:C6H12O5
Weight:Average: 164.1565
Monoisotopic: 164.068473494
InChI Key:PNNNRSAQSRJVSB-BXKVDMCESA-N
InChI:InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
CAS number:3615-41-6
IUPAC Name:(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Traditional IUPAC Name:6-deoxy-L-mannose
SMILES:[H][C@@](C)(O)[C@]([H])(O)[C@@]([H])(O)[C@@]([H])(O)C=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain aldehyde
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:122 C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility258 g/LALOGPS
logP-2ALOGPS
logP-2.5ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)12.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.8 m³·mol⁻¹ChemAxon
Polarizability15.24 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
alpha-L-Rhamnose + L-Rhamnose <> L-Rhamnulose
SMPDB Pathways:Not Available
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-014i-0920000000-3f32654cd6b207d5192cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-014i-0910000000-3efed9ba21b4acc1a0a7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-15cadd38d19e98599380View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-845777ce5ccb02564dd4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-a3998948f1f154365feaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-09ff33efc7ead61776acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c17a9df600308d9b31beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-0a4i-9300000000-aba9c0e75315919d15caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 2V, negativesplash10-03di-0900000000-5bc4a1e81d1743e4d888View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, negativesplash10-114r-4900000000-cce3aaf678cc70d6861aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-0pb9-9700000000-4f6230f5365dba6dd52fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-0a4i-9100000000-9477982822aed3518682View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-0a4i-9000000000-594366ab16c0cac99671View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-0a4i-9000000000-f0b38b5601df3611821cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0udi-3900000000-a5276b0d1c6f7703894fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-004i-2900000000-2a20cb5f730a3fd74448View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0089-9000000000-643fd0369e6935a5767cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0532-9400000000-2e4332a61dcaf8add5aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-ff3539fb021325c23c4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9200000000-b270b5d83d44008211baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f516852459b277fdb157View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ly9-9600000000-efc90d58c6475abfcecdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9100000000-3b89500afd7b488df6faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7b10fe17f3ce9401fd3fView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID62346
HMDB IDHMDB00849
Pubchem Compound ID25310
Kegg IDC00507
ChemSpider IDNot Available
WikipediaRhamnose
BioCyc IDNot Available
EcoCyc IDNot Available
Ligand ExpoRNS

Enzymes

Protein Details
1. L-rhamnose isomerase
General function:
Involved in L-rhamnose isomerase activity
Specific function:
L-rhamnose = L-rhamnulose
Gene Name:
rhaA
Uniprot ID:
P32170
Molecular weight:
47199
Reactions
L-rhamnose = L-rhamnulose.